Construction of Supramolecular Self-Assemblies Based on the Biamphiphilic Ionic Liquid−β-Cyclodextrin System

Abstract

A new kind of biamphiphilic ionic liquid (BAIL) consisting of 1-dodecyl-3-methylimidazolium (C12mim(+)) and dodecyl sulfonate (DSN(-)) has been synthesized and characterized for the investigation on its self-assembling behavior with β-CD in the aqueous medium. Vesicles were found in the diluted C12mimDSN@3β-CD solution, and on increasing the concentrations of both IL and β-CD, the solution turned into a white hydrogel, which showed a temperature-dependent sol-gel transition. The building block consisting of one C12mimDSN and three β-CDs was proposed, and a novel self-assembly mechanism was studied. Both cation and anion of the BAIL are involved in the self-assembling with β-CD. The electronic interaction between C12mim(+) and DSN(-), the hydrophobic interaction between the alkyl chains of BAIL and β-CD cavity, H-bond between neighboring β-CDs, and the interaction between imidazolium headgroup and water in the hydrogel are the driving force for the self-assembly.

Secondary assembly mechanism of cyclodextrin based on LiNTf2@β-CD system

“…The signals in Fig. 1b and d, whose diameter is about 1-2 nm, probably derive from b-CD or the NTf 2 --b-CD inclusion complex [22,23,42]. In addition, LiNTf 2 on its own cannot selfassembly so that no self-assembly signal occurs in Fig.…”

“…Before freeze-drying, the solutions were quickly freezed by liquid nitrogen to maintain their original self-assembly structure [41,42].…”

“…Our research group has been investigating the supramolecular interaction pattern between ionic liquids (ILs) and CDs [37][38][39][40], and constructed vesicles and supramolecular hydrogel between ILs and CDs [41,42]. In our previous studies about the interaction between the IL 1-alkyl-3-methylimidazolium-bis(trifluoromethylsulfonyl) imide (C n mimNTf 2 ) and b-CD, we reported that NTf 2 -could form inclusion complex with b-CD in the diluted aqueous solution [38,39].…”

Hydrophobically Driven Morphologically Diverse Self-Assembled Architectures of Deoxycholate and Imidazolium-Based Biamphiphilic Ionic Liquids in Aqueous Medium

“…The effect of nature of different counterions on self-assembly behavior has also been reported . The nature of both cation and anion influences the aggregation behavior of SAILs, governed through mutual binding capacity, hydrophobicity, and size of cation and anion, and studies on self-assembly behavior of imidazolium-based SAILs having aromatic counterions have been derived. , To have synergetic interactions similar to those exhibited by cat-anionic systems giving rise to better surface activity, − not present in either cationic or anionic surfactant, biamphiphilic SAILs (BAILs) comprising amphiphilic cation and anion were reported. − This not only led to enhanced surface activity but also offered less complex systems than cat-anionic ones, which contains the counterions of respective surfactants in the colloidal system. Therefore, we conceptualize to synthesize and investigate the aggregation behavior of new BAILs based on imidazolium cations, [C n mim] + , and deoxycholate anion, [DC] − , in expectation of high surface activity and control over the structure of formed aggregates via minor alterations in length of alkyl chain of [C n mim] + .…”

Supramolecular assemblies of azobenzene‐β‐cyclodextrin dimers and azobenzene modified polycaprolactones

“…Comparely, in DMSO, AZO‐β‐CD dimers are preferred to mono‐disperse (Figure S4) . When amphiphilic molecular AZO‐β‐CD dimers are dissolved in aqueous solution, a typical tyndall phenomenon of AZO‐β‐CD solution is detected when a laser pointer is used to light the sample . To obtain more information about the aggregate behaviors of the elaborately synthesized molecule, we perform SEM experiments with the sample casted on a silicon wafer.…”